Structure Database (LMSD)
Common Name
11R-HETE
Systematic Name
11R-hydroxy-5Z,8Z,12E,14Z-eicosatetraenoic acid
Synonyms
- 11(R)-HETE
3D model of 11R-HETE
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
11(R)-HETE is an oxylipin produced by COX-1 and COX-2 from arachidonic acid or aspirin-acetylated COX-2-mediated oxidation of arachidonic acid.1,2 It is also produced by 11(R)-lipoxygenases in the freshwater hydra (H. vulgaris), where it is involved in tentacle regeneration, and in the sea urchin (S. purpuratus).3,4
This information has been provided by Cayman Chemical
References
1. Thuresson, E.D., Lakkides, K.M., and Smith, W.L. Different catalytically competent arrangements of arachidonic acid within the cyclooxygenase active site of prostaglandin endoperoxide H synthase-1 lead to the formation of different oxygenated products. J. Biol. Chem. 275(12), 8501-8507 (2000).
4. Hawkins, D.J., and Brash, A.R. Eggs of the sea urchin, Strongylocentrotus purpuratus, contain a prominent (11R) and (12R) lipoxygenase activity. J. Biol. Chem. 262(16), 7629-7634 (1987).
String Representations
InChiKey (Click to copy)
GCZRCCHPLVMMJE-WXMXURGXSA-N
InChi (Click to copy)
InChI=1S/C20H32O3/c1-2-3-4-5-7-10-13-16-19(21)17-14-11-8-6-9-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b9-6-,10-7-,14-11-,16-13+/t19-/m0/s1
SMILES (Click to copy)
C(/C[C@@H](O)/C=C/C=C\CCCCC)=C/C/C=C\CCCC(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
23
Rings
0
Aromatic Rings
0
Rotatable Bonds
14
Van der Waals Molecular Volume
367.73
Topological Polar Surface Area
57.53
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
3
logP
5.47
Molar Refractivity
97.94
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Updated at
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